One of the most imaginative and unorthodox artists in Renaissance Florence, Piero di Cosimo, like many painters, came under the spell of Leonardo da Vinci. In their dense grouping and shadowy presentation, the figures in this work reflect the "dark manner" of that famous older master. Gathered around the Virgin and Child are a pair of wingless angels and two saints—John the Baptist, who eagerly offers plums to Christ, and Cecilia, who holds a sheet with musical notations and appears to be singing to him. Both gestures are unusual for a painting of this period.

Round pictures, or tondi, were typically created for the bedroom of a wealthy patron (circular frames were very expensive) and usually celebrated the birth of a child—in this case, perhaps to a woman named Cecilia.